Issue 26, 2022

Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide

Abstract

A metal- and base-free 5-endo-trig sulfonylative cyclization between 1,5-dienes, aryldiazonium salts and SO2 (from SOgen) is presented. This method could successfully produce sulfonylated pyrrolin-2-ones in one pot with excellent regioselectivity and good-to-excellent yields. This strategy features mild reaction conditions and broad substrate scope. Moreover, a scale-up reaction and three synthetic applications demonstrate the practicality of this method. Lastly, control experiments indicate that the 5-endo-trig sulfonylative cyclization may proceed in a radical pathway.

Graphical abstract: Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide

Supplementary files

Article information

Article type
Paper
Submitted
13 mai 2022
Accepted
31 mai 2022
First published
06 juin 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 16745-16750

Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide

X. Wang, F. You, B. Xiong, L. Chen, X. Zhang and Z. Lian, RSC Adv., 2022, 12, 16745 DOI: 10.1039/D2RA03034A

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